EP2222736A1 - High water content silicone hydrogels - Google Patents
High water content silicone hydrogelsInfo
- Publication number
- EP2222736A1 EP2222736A1 EP20080858010 EP08858010A EP2222736A1 EP 2222736 A1 EP2222736 A1 EP 2222736A1 EP 20080858010 EP20080858010 EP 20080858010 EP 08858010 A EP08858010 A EP 08858010A EP 2222736 A1 EP2222736 A1 EP 2222736A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- silicone
- weight percent
- monomer
- water content
- silicone hydrogel
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 108
- 239000000017 hydrogel Substances 0.000 title claims abstract description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 239000000178 monomer Substances 0.000 claims abstract description 128
- 239000000203 mixture Substances 0.000 claims abstract description 76
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 20
- -1 silylalkyl methacrylate Chemical compound 0.000 claims description 71
- 229910052760 oxygen Inorganic materials 0.000 claims description 36
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 31
- 239000001301 oxygen Substances 0.000 claims description 31
- 230000035699 permeability Effects 0.000 claims description 23
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 14
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 11
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 11
- JZUCDZZFJRODNS-UHFFFAOYSA-N (4-tert-butyl-2-hydroxycyclohexyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCC(C(C)(C)C)CC1O JZUCDZZFJRODNS-UHFFFAOYSA-N 0.000 claims description 10
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 9
- 239000007983 Tris buffer Substances 0.000 claims description 7
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 5
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical group CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 5
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 5
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 4
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 claims description 4
- BSCJIBOZTKGXQP-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCO BSCJIBOZTKGXQP-UHFFFAOYSA-N 0.000 claims description 4
- BOURDYMMTZXVRY-UHFFFAOYSA-N 2-(2-methylprop-2-enoylamino)acetic acid Chemical compound CC(=C)C(=O)NCC(O)=O BOURDYMMTZXVRY-UHFFFAOYSA-N 0.000 claims description 3
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 239000004471 Glycine Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 26
- 150000003254 radicals Chemical class 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 125000002091 cationic group Chemical group 0.000 description 21
- 125000003118 aryl group Chemical group 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 239000000523 sample Substances 0.000 description 19
- 230000002209 hydrophobic effect Effects 0.000 description 17
- 239000000463 material Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- 125000000753 cycloalkyl group Chemical group 0.000 description 13
- 238000009472 formulation Methods 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- 239000010703 silicon Substances 0.000 description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 description 7
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 7
- 239000002953 phosphate buffered saline Substances 0.000 description 7
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000004809 Teflon Substances 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- 210000004087 cornea Anatomy 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229920005604 random copolymer Polymers 0.000 description 4
- 238000005728 strengthening Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000004407 fluoroaryl group Chemical group 0.000 description 3
- 210000004379 membrane Anatomy 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical compound NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 125000005401 siloxanyl group Chemical group 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- KTHMJTVOQULJOJ-UHFFFAOYSA-N (2,3-dimethyl-3-phenylsilyloxysilylbutan-2-yl) acetate Chemical compound C(C)(=O)OC(C([SiH2]O[SiH2]C1=CC=CC=C1)(C)C)(C)C KTHMJTVOQULJOJ-UHFFFAOYSA-N 0.000 description 1
- OVCIIUBCDQDGHY-UHFFFAOYSA-N (4-ethenylphenyl) carbamate Chemical compound NC(=O)OC1=CC=C(C=C)C=C1 OVCIIUBCDQDGHY-UHFFFAOYSA-N 0.000 description 1
- SADSZVISBKSAKG-UHFFFAOYSA-N (4-tert-butyl-2-hydroxycyclopentyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CC(C(C)(C)C)CC1O SADSZVISBKSAKG-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- KQAQJORNWGFUKW-UHFFFAOYSA-N 1-(2-ethenoxyethyl)piperidine Chemical compound C=COCCN1CCCCC1 KQAQJORNWGFUKW-UHFFFAOYSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- IEPUABWMJBVAAN-UHFFFAOYSA-N 2-[4-[[4-[4-[2-(2-methylprop-2-enoyloxy)ethyl]anilino]-9,10-dioxoanthracen-1-yl]amino]phenyl]ethyl 2-methylprop-2-enoate Chemical compound C1=CC(CCOC(=O)C(=C)C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(CCOC(=O)C(C)=C)C=C1 IEPUABWMJBVAAN-UHFFFAOYSA-N 0.000 description 1
- NPPNUGUVBUJRAB-UHFFFAOYSA-N 2-[tert-butyl(dimethyl)silyl]oxyethyl ethenyl carbonate Chemical compound CC(C)(C)[Si](C)(C)OCCOC(=O)OC=C NPPNUGUVBUJRAB-UHFFFAOYSA-N 0.000 description 1
- QYWKGACXENPUKU-UHFFFAOYSA-N 2-ethenoxycarbonyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)OC=C QYWKGACXENPUKU-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- MNZNJOQNLFEAKG-UHFFFAOYSA-N 2-morpholin-4-ylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCN1CCOCC1 MNZNJOQNLFEAKG-UHFFFAOYSA-N 0.000 description 1
- 125000006088 2-oxoazepinyl group Chemical group 0.000 description 1
- 125000004638 2-oxopiperazinyl group Chemical group O=C1N(CCNC1)* 0.000 description 1
- 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 description 1
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical compound NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- 125000005986 4-piperidonyl group Chemical group 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 125000000172 C5-C10 aryl group Chemical group 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
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- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 229910004679 ONO2 Inorganic materials 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 206010042674 Swelling Diseases 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229920006311 Urethane elastomer Polymers 0.000 description 1
- HMACJMNLCAEFAD-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl] 2-methylbut-2-enoate Chemical compound CC=C(C)C(=O)O[Si](C)(C)O[Si](C)(C)C HMACJMNLCAEFAD-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001253 acrylic acids Chemical class 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 229920006318 anionic polymer Polymers 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000002785 azepinyl group Chemical group 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000005872 benzooxazolyl group Chemical group 0.000 description 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 239000003618 borate buffered saline Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000013590 bulk material Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000005507 decahydroisoquinolyl group Chemical group 0.000 description 1
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- AXBQZEBDCBCYAZ-UHFFFAOYSA-N ethenyl (4-ethenylphenyl) carbonate Chemical compound C=COC(=O)OC1=CC=C(C=C)C=C1 AXBQZEBDCBCYAZ-UHFFFAOYSA-N 0.000 description 1
- KZJNAICCMJTRKF-UHFFFAOYSA-N ethenyl 2-trimethylsilylethyl carbonate Chemical compound C[Si](C)(C)CCOC(=O)OC=C KZJNAICCMJTRKF-UHFFFAOYSA-N 0.000 description 1
- RWEUKWCZWYHIQA-UHFFFAOYSA-N ethenyl 3-trimethylsilylpropyl carbonate Chemical compound C[Si](C)(C)CCCOC(=O)OC=C RWEUKWCZWYHIQA-UHFFFAOYSA-N 0.000 description 1
- BHBDVHVTNOYHLK-UHFFFAOYSA-N ethenyl 3-tris(trimethylsilyloxy)silylpropylsulfanylformate Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)CCCSC(=O)OC=C BHBDVHVTNOYHLK-UHFFFAOYSA-N 0.000 description 1
- ILHMPZFVDISGNP-UHFFFAOYSA-N ethenyl n-[3-tris(trimethylsilyloxy)silylpropyl]carbamate Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)CCCNC(=O)OC=C ILHMPZFVDISGNP-UHFFFAOYSA-N 0.000 description 1
- KRAZQXAPJAYYJI-UHFFFAOYSA-N ethenyl trimethylsilylmethyl carbonate Chemical compound C[Si](C)(C)COC(=O)OC=C KRAZQXAPJAYYJI-UHFFFAOYSA-N 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- IHBKAGRPNRKYAO-UHFFFAOYSA-M methyl sulfate;trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium Chemical compound COS([O-])(=O)=O.CC(=C)C(=O)OCC[N+](C)(C)C IHBKAGRPNRKYAO-UHFFFAOYSA-M 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 description 1
- QRWZCJXEAOZAAW-UHFFFAOYSA-N n,n,2-trimethylprop-2-enamide Chemical compound CN(C)C(=O)C(C)=C QRWZCJXEAOZAAW-UHFFFAOYSA-N 0.000 description 1
- NDUQVWKRPWJZIM-UHFFFAOYSA-N n-(4-tert-butyl-2-hydroxycyclohexyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC1CCC(C(C)(C)C)CC1O NDUQVWKRPWJZIM-UHFFFAOYSA-N 0.000 description 1
- STRWAOXFHCTTQE-UHFFFAOYSA-N n-[2-hydroxy-5-(4-methylpentyl)cyclopentyl]-2-methylprop-2-enamide Chemical compound CC(C)CCCC1CCC(O)C1NC(=O)C(C)=C STRWAOXFHCTTQE-UHFFFAOYSA-N 0.000 description 1
- GORGQKRVQGXVEB-UHFFFAOYSA-N n-ethenyl-n-ethylacetamide Chemical compound CCN(C=C)C(C)=O GORGQKRVQGXVEB-UHFFFAOYSA-N 0.000 description 1
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- XNTUJOTWIMFEQS-UHFFFAOYSA-N octadecanoyl octadecaneperoxoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCCCCCCCC XNTUJOTWIMFEQS-UHFFFAOYSA-N 0.000 description 1
- 125000005060 octahydroindolyl group Chemical group N1(CCC2CCCCC12)* 0.000 description 1
- 125000005061 octahydroisoindolyl group Chemical group C1(NCC2CCCCC12)* 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
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- 230000003647 oxidation Effects 0.000 description 1
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- 125000004043 oxo group Chemical group O=* 0.000 description 1
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
- 229920005597 polymer membrane Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- 238000009877 rendering Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
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- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
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- 239000000758 substrate Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
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- 238000004381 surface treatment Methods 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000006089 thiamorpholinyl sulfoxide group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Definitions
- the present invention generally relates to high water content silicone hydrogel materials. Description of the Related Art
- Hydrogels represent a desirable class of materials for contact lenses.
- a hydrogel is a hydrated cross-linked polymeric system that contains water in an equilibrium state.
- Hydrogel lenses offer relatively high oxygen permeability as well as desirable biocompatibility and comfort.
- Oxygen permeability is one important factor in contact lens design to maintain ocular health for contact lens wearers.
- a contact lens must allow oxygen to reach the cornea in an amount which is sufficient for long-term corneal health.
- the contact lens must also allow oxygen from the surrounding air to reach the cornea because the cornea does not receive oxygen from the blood supply like other tissue.
- Soft contact lenses conform closely to the shape of the eye, so oxygen cannot easily circumvent the lens. Thus, soft contact lenses must allow oxygen to diffuse through the lens to reach the cornea.
- Another ophthalmic compatibility requirement for soft contact lenses is that the lens must not strongly adhere to the eye.
- the consumer must be able to easily remove the lens from the eye for disinfecting, cleaning, or disposal.
- the lens must also be able to move on the eye in order to encourage tear flow between the lens and the eye. Tear flow between the lens and eye allows for debris, such as foreign particulates or dead epithelial cells, to be swept from beneath the lens and, ultimately, out of the tear fluid.
- a contact lens must not adhere to the eye so strongly that adequate movement of the lens on the eye is inhibited.
- high water content conventional hydrogel contact lenses composed of copolymers of hydrophilic monomers such as 2- hydroxyethyl methacrylate) (HEMA), N-vinylpyrrolidone and the like, and prepared by lathe-cutting methods, spin casting methods, cast molding methods or combinations thereof, followed by a swelling treatment in a physiological saline and/or phosphate buffer solution to obtain lenses with water contents of about 20% to about 80% by weight were developed.
- HEMA 2- hydroxyethyl methacrylate
- N-vinylpyrrolidone N-vinylpyrrolidone
- Prior art soft silicon-containing hydrophilic contact lenses with higher water contents tend to have reduced or lower oxygen permeabilities.
- a silicone hydrogel contact lens available under the tradename, Focus Night & Day (available from CIBA Vision Corporation), has a water content of about 24% and a Dk of about 140 Barrers.
- Another silicone hydrogel contact lens available under the tradename, 02 Optix (available from CIBA Vision Corporation), has a water content of about 33% and a Dk of about 1 10 Barrers.
- Another silicone hydrogel contact lens available under the tradename, Acuvue Oasys available from Johnson & Johnson
- a non-silicone hydrogel contact lens available under the tradename, Acuvue2 available from Johnson & Johnson
- U.S. Patent No. 5,260,000 discloses a process for preparing silicone hydrogel contact lenses, where silicone hydrogel contact lenses are cast from monomeric mixtures including a major amount of a silicone-containing monomer, a hydrophilic monomer and n-nonanol or n-hexanol as a diluent, and subsequently extracted with isopropanol to remove any remaining diluent as well as unreacted monomers and oligomers.
- problems associated with the manufacturing of low cost lenses from silicone hydrogels include the need for a solvent extraction step in the manufacturing process to remove any unreacted silicone as well as the need to perform a post-polymerization surface modification step(s) to provide a wettable, lubricious and low-fouling surface.
- U.S. Patent No. 7,268, 198 discloses a silicone hydrogel that is the hydrated polymerization product of a monomer mixture comprising a hydrophilic monomer selected from the group consisting of N-vinyl-N-methyl acetamide, N-vinyl-N- ethyl acetamide, N-vinyl-N-ethyl formamide, N-vinyl formamide, N-vinyl pyrrolidone and mixtures thereof, and a polysiloxane-containing monomer, wherein the hydrogel has an oxygen permeability of at least about 120 Barrers and a modulus from 40 to 57 g/mnr.
- each of the examples in the ' 198 patent form a silicone hydrogel having a water content between 19.2% and 35.3%.
- a silicone hydrogel formed from the hydrated polymerization product of a monomer mixture comprising (a) a major amount of a non-silicone-containing hydrophilic monomer; and (b) a minor amount of a silicone-containing monomer, wherein the hydrogel has a water content of greater than 50 weight percent is provided.
- a silicone hydrogel formed from the hydrated polymerization product of a monomer mixture comprising (a) a major amount of a non-silicone-containing hydrophilic monomer; and (b) a minor amount of a silicone-containing monomer, wherein the hydrogel has a water content of greater than 70 weight percent and an oxygen permeability of about 30 to about 70 Barrers is provided.
- a contact lens comprising a silicone hydrogel formed from the hydrated polymerization product of a monomer mixture comprising (a) a major amount of a non-silicone- containing hydrophilic monomer; and (b) a minor amount of a silicone-containing monomer, wherein the hydrogel has a water content of greater than 50 weight percent.
- the silicone-containing monomer By employing a minor amount of a silicone-containing monomer to a base material comprising a major amount of a non-silicone-containing hydrophilic monomer in the preparation of a silicone hydrogel, the silicone-containing monomer will have substantially no effect on the properties of the bulk material (e.g., oxygen permeability, water content, modulus, etc.) and surface properties (e.g., wettability, lubricity, etc.) thereof.
- the silicone hydrogels of the present invention can advantageously be formed with a desirable hydrophilic surface and high water content without any solvent extraction or post-polymerization surface treatment steps while also having suitable oxygen permeability properties. In this manner, a silicone hydrogel can be manufactured in a relatively efficient process and on a low-cost platform.
- the present invention is directed to silicone hydrogels formed from the hydrated polymerization product of a monomer mixture comprising (a) a major amount of a non- silicone -containing hydrophilic monomer; and (b) a minor amount of a silicone- containing monomer, wherein the hydrogel has a water content of greater than 50 weight percent.
- a monomer mixture comprising (a) a major amount of a non- silicone -containing hydrophilic monomer; and (b) a minor amount of a silicone- containing monomer, wherein the hydrogel has a water content of greater than 50 weight percent.
- the term "monomer” denotes relatively low molecular weight compounds that are polymerizable by free radical polymerization, as well as higher molecular weight compounds also referred to as “prepolymers”, “macromonomers”, and similar terms.
- Suitable non-silicone-containing hydrophilic monomers include, but are not limited to, unsaturated carboxylic acids, such as (meth)acrylic acids; (meth)acrylic substituted alcohols, vinyl lactams, (meth)acrylamides and the like.
- unsaturated carboxylic acids such as (meth)acrylic acids; (meth)acrylic substituted alcohols, vinyl lactams, (meth)acrylamides and the like.
- (meth) denotes an optional methyl substituent.
- terms such as “(meth)acrylate” denotes either methacrylate or acrylate
- (meth)acrylamide” denotes either methacrylamide or acrylamide.
- non-silicone- containing hydrophilic monomers include methacrylamide, N-methylmethacrylamide, N,N-dimethylacrylamide, N,N-dimethylmethylacrylamide, glyceryl methacrylate, N-(2- hydroxyethyl)methacrylamide, N-methacryloyl glycine; and (2-hydroxy-3- methacryloylpropyl)-4-methoxy phenylether.
- Preferred monomers include N,N- dimethylacrylamide, N-vinyl-2-pyrrolidone (NVP), 2-hydroxyethyl methacrylate (HEMA) and mixtures thereof.
- the non-silicone-containing hydrophilic monomer is included in the monomeric mixture in a major amount (a term which is meant to include mixtures of hydrophilic monomers), i.e., an amount of at least about 50 parts by weight of total components in the monomelic mixture.
- the non-silicone-containing hydrophilic monomer is present in the monomeric mixture in an amount ranging from about 50 to about 95 parts by weight of total monomeric mixture components with about 60 to about 90 parts by weight being especially preferred.
- the monomeric mixture will include at least about 60 parts by weight, and more preferably at least about 80 parts by weight, of total non-silicone-containing hydrophilic monomeric components so that the resultant silicone hydrogel is predominantly hydrophilic and wettable for use as a silicone hydrogel material.
- the silicon-containing monomer can be any polymerizable silicon-containing monomer.
- the monomers may be added to the monomeric mixture from which a shaped article is obtained as monomers or prepolymers.
- the terms "silicone-containing monomers” and "hydrophilic monomers” include prepolymers.
- the silicone-containing monomers can be non-ionic silicone-containing monomers. Applicable silicone-containing monomeric units for use in the formation of silicone hydrogels are well known in the art and numerous examples are provided in U.S. Patent Nos. 4,136,250; 4,153,641 ; 4,740,533; 5,034,461; 5,070,215; 5,260,000; 5,310,779; and 5,358,995.
- silicon-containing monomeric units include bulky siloxanyl monomers represented by the structure of Formula I:
- X denotes — O — or — NR" — , wherein R" is hydrogen, methyl or ethyl; each R independently denotes hydrogen or methyl; each R independently denotes a lower alkyl radical, phenyl radical or a group represented by
- each R'" independently denotes a lower alkyl or phenyl radical; and h is 1 to 10.
- Examples of bulky monomers are 3-methacryloyloxypropyltris(trimethyl- siloxy)silane or tris(trimethylsiloxy)silylpropyl methacrylate, sometimes referred to as TRIS and tris(trimethylsiloxy)silylpropyl vinyl carbamate, sometimes referred to as TRIS-VC, pentamethyldisiloxanyl methylmethacrylate, phenyltetramethyl- disiloxanylethyl acetate, and methyldi(trimethylsiloxy)rnethacryloxyrnethyl silane and the like and mixtures thereof.
- the silicone-containing monomer is a tris(trialkylsiloxy)silylalkyl methacrylate-containing monomer such as a tris(trimethylsiloxy)silylpropyl methacrylate-containing monomer.
- Such bulky monomers may be copolymerized with a silicone macromonomer, such as a poly(organosiloxane) capped with an unsaturated group at two or more ends of the molecule.
- a silicone macromonomer such as a poly(organosiloxane) capped with an unsaturated group at two or more ends of the molecule.
- U.S. Patent No. 4, 153,641 discloses, for example, various unsaturated groups such as acryloyloxy or methacryloyloxy groups.
- silicone-containing monomers includes, but is not limited to, silicone-containing vinyl carbonate or vinyl carbamate monomers such as, for example, 1 ,3-bis[4-vinyloxycarbonyloxy)but- 1 -yl]tetramethyl-disiloxane; 3- (trimethylsilyl)propyl vinyl carbonate; 3-(vinyloxycarbonylthio)propyl- [tris(trimethylsiloxy)silane]; 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbamate; 3- [tris(trimethylsiloxy)silyl]propyl allyl carbamate; 3-[tris(trimethylsiloxy)silyl] ⁇ ropyl vinyl carbonate; t-butyldimethylsiloxyethyl vinyl carbonate; trimethylsilylethyl vinyl carbonate; trimethylsilylmethyl vinyl carbonate, "V 2 D 25 " of the general formula
- silicon-containing monomers includes polyurethane- polysiloxane macromonomers (also sometimes referred to as prepolymers), which may have hard-soft-hard blocks like traditional urethane elastomers. They may be end- capped with a hydrophilic monomer such as 2-hydroxyethyl methacrylate (HEMA).
- HEMA 2-hydroxyethyl methacrylate
- silicone urethanes are disclosed in a variety or publications, including PCT Published Application No. WO 96/31792 discloses examples of such monomers, which disclosure is hereby incorporated by reference in its entirety.
- Representative examples of silicone urethane monomers are represented by Formulae II and III: E(*D*A*D*G) a *D*A*D*E'; or (II)
- D independently denotes an alkyl diradical, an alkyl cycloalkyl diradical, a cycloalkyl diradical, an aryl diradical or an alkylaryl diradical having 6 to about 30 carbon atoms;
- G independently denotes an alkyl diradical, a cycloalkyl diradical, an alkyl cycloalkyl diradical, an aryl diradical or an alkylaryl diradical having 1 to about 40 carbon atoms and which may contain ether, thio or amine linkages in the main chain;
- * denotes a urethane or ureido linkage; a is at least 1;
- A independently denotes a divalent polymeric radical of Formula IV:
- each R s independently denotes an alkyl or fluoro-substituted alkyl group having 1 to about 10 carbon atoms which may contain ether linkages between the carbon atoms; m' is at least 1; and p is a number that provides a moiety weight of about 400 to about 10,000; each of E and E' independently denotes a polymerizable unsaturated organic radical represented by Formula V:
- R >3 is hydrogen or methyl
- R 4 is hydrogen, an alkyl radical having 1 to 6 carbon atoms, or a — CO — Y — R 6 radical wherein Y is — O— , — S— or -NH-;
- R 1 is a divalent alkylene radical having 1 to about 10 carbon atoms
- R 6 is a alkyl radical having 1 to about 12 carbon atoms
- X denotes —CO— or -OCO-
- Z denotes — O — or — NH — ;
- Ar denotes an aromatic radical having about 6 to about 30 carbon atoms; w is 0 to 6; x is 0 or 1 ; y is 0 or 1 ; and z is 0 or 1.
- a preferred silicone-containing urethane monomer is represented by Formula VI:
- m is at least 1 and is preferably 3 or 4
- a is at least 1 and preferably is 1
- p is a number which provides a moiety weight of about 400 to about 10,000 and is preferably at least about 30
- R 7 is a diradical of a diisocyanate after removal of the isocyanate group, such as the diradical of isophorone diisocyanate
- each E" is a group represented by:
- the silicone-containing monomers is a cationic silicone-containing monomer.
- Representative examples of applicable cationic silicon-containing monomeric units include cationic monomers of Formula VII:
- each L independently can be an urethane, carbonate, carbamate, carboxyl ureido, sulfonyl, straight or branched C 1 -C30 alkyl group, straight or branched C 1 -C 30 fluoroalkyl group, ester-containing group, ether-containing group, polyether-containing group, ureido group, amide group, amine group, substituted or unsubstituted C 1 -C 30 alkoxy group, substituted or unsubstituted C 3 -C 30 cycloalkyl group, substituted or unsubstituted C 3 -C 30 cycloalkylalkyl group, substituted or unsubstituted C 3 -C 30 cycloalkylalkyl group, substituted or unsubstituted C 3 -C 30 cycloalkenyl group, substituted or unsubstituted C5-C30 aryl group, substituted or unsubstituted C5-C
- X " is at least a single charged counter ion.
- single charge counter ions include the group consisting of Cl “ , Br “ , I ' , CF 3 CO 2 " , CH 3 CO 2 “ , HCO 3 " , CH 3 SO 4 " , /?- toluenesulfonate, HSO 4 5 H 2 PO 4 " , NO 3 " , and CH 3 CH(OH)CO 2 " .
- Examples of dual charged counter ions would include SO 4 " “ , CO 3 2” and HPO 4 ' “ .
- Other charged counter ions would be obvious to one of ordinary skill in the art. It should be understood that a residual amount of counter ion may be present in the hydrated product.
- Ri and R 2 are each independently hydrogen, a straight or branched C 1 -C30 alkyl group, straight or branched C 1 -C 30 fluoroalkyl group, C 1 -C 20 ester group, ether containing group, polyether containing group, ureido group, amide group, amine group, substituted or unsubstituted C 1 -C 30 alkoxy group, substituted or unsubstituted C3-C 30 cycloalkyl group, substituted or unsubstituted C 3 -C 30 cycloalkylalkyl group, substituted or unsubstituted C 3 -C 30 cycloalkylalkyl group, substituted or unsubstituted C 3 -C 30 cycloalkenyl group, substituted or unsubstituted C 5 -C 1 0 aryl group, substituted or unsubstituted C5-C3 0 arylalkyl group, substituted or unsubstit
- each Ri is the same and is -OSi(CH 3 ) 3 R 2 is methyl, Li is an alkyl amide, L 2 is a alkyl amide or ester having 2 or 3 carbon atoms that is joined to a polyme ⁇ zable vinyl group, R 3 is methyl, R 4 is H and X is Br or Cl
- Further preferred structures have the following structural Formulae IX-XIII: and A schematic representation of synthetic methods for making a cationic silicon- containing monomer as disclosed hereinabove is provided below:
- cationic silicon-containing monomeric units for use herein include cationic monomers of Formula XIV:
- each L can be the same or different and is as defined above for L in Formula VII;
- X " is at least a single charged counter ion as defined above for X " in Formula VII;
- R 5 , R ⁇ , R7, R8, R9, Rio, Ri 1 and Rn are each independently as defined above for Ri in Formula VII;
- V is independently a polymerizable ethylenically unsaturated organic radical and n is an integer of 1 to about 300.
- Preferred monomers of Formula XIV are shown in Formulae XV-XIX below:
- cationic silicon-containing monomeric units for use herein include cationic monomers of Formula XX:
- each L can be the same or different and is as defined above for L in Formula VII;
- X " is at least a single charged counter ion as defined above for X " in Formula VII;
- each Ri, R n and R M are independently as defined above for Ri in Formula VII and
- A is a polymerizable vinyl moiety.
- a preferred cationic random copolymer of Formula XX is shown in Formula XXI below:
- x is 0 to 1000 and y is 1 to 300.
- cationic random copolymers of Formula XXII wherein x is 0 to 1000, y is 1 to 300; each R ⁇ and Ri 6 can be the same or different and can be the groups as defined above for Ri in Formula VII; Rn is independently one or more of the following Formulae XXIII and XXIV:
- L can be the same or different and is as defined above for L in Formula VII;
- X " is at least a single charged counter ion as defined above for X " in Formula VII;
- Ri 8 can be the same or different and can be the groups as defined above for R 1 in Formula VII; and
- Ri 9 is independently hydrogen or methyl.
- a schematic representation of a synthetic method for preparing cationic silicon- containing random copolymers such as poly(dimethylsiloxane) bearing pendant polyme ⁇ zable cationic groups disclosed herein is provided below.
- urethanes for use herein include, by way of example, a secondary amine linked to a carboxyl group which may also be linked to a further group such as an alkyl. Likewise the secondary amine may also be linked to a further group such as an alkyl.
- carbonates for use herein include, by way of example, alkyl carbonates, aryl carbonates, and the like.
- carbamates for use herein include, by way of example, alkyl carbamates, aryl carbamates, and the like.
- carboxyl ureidos for use herein include, by way of example, alkyl carboxyl ureidos, aryl carboxyl ureidos, and the like.
- sulfonyls for use herein include, by way of example, alkyl sulfonyls, aryl sulfonyls, and the like.
- alkyl groups for use herein include, by way of example, a straight or branched hydrocarbon chain radical containing carbon and hydrogen atoms of from 1 to about 18 carbon atoms with or without unsaturation, to the rest of the molecule, e.g., methyl, ethyl, n-propyl, 1-methylethyl (isopropyl), n-butyl, n- pentyl, etc., and the like.
- fluoroalkyl groups for use herein include, by way of example, a straight or branched alkyl group as defined above having one or more fluorine atoms attached to the carbon atom, e.g., -CF 3 , -CF 2 CF 3 , -CH 2 CF 3 , -CH 2 CF 2 H, - CF 2 H and the like.
- ester groups for use herein include, by way of example, a carboxylic acid ester having one to 20 carbon atoms and the like.
- ether or polyether-containing groups for use herein include, by way of example, an alkyl ether, cycloalkyl ether, cycloalkylalkyl ether, cycloalkenyl ether, aryl ether, arylalkyl ether wherein the alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, aryl, and arylalkyl groups are as defined herein, e.g., alkylene oxides, poly(alkylene oxide)s such as ethylene oxide, propylene oxide, butylene oxide, poly(ethylene oxide)s, poly(ethylene glycol)s, poly(propylene oxide)s, poly(butylene oxide)s and mixtures or copolymers thereof, an ether or polyether group of the general formula -R 20 OR
- amide groups for use herein include, by way of example, an amide of the general formula -R 23 C(O)NR 24 R 25 wherein R 23 , R 24 and R 25 are independently Q-C 30 hydrocarbons, e.g., R 23 can be an alkylene group, arylene group, cycloalkylene group and R 24 and R 25 can be an alkyl groups, aryl group, and cycloalkyl group as defined herein and the like.
- amine groups for use herein include, by way of example, an amine of the general formula -R 26 NR 27 R 2 S wherein R 26 is a C 2 -Q O alkylene, arylene, or cycloalkylene and R 27 and R 2 s are independently C 1 -C 30 hydrocarbons such as, for example, alkyl groups, aryl groups, or cycloalkyl groups as defined herein, and the like.
- an ureido group for use herein include, by way of example, an ureido group having one or more substituents or unsubstituted ureido.
- the ureido group preferably is an ureido group having 1 to 12 carbon atoms.
- substituents include alkyl groups and aryl groups.
- the ureido group include 3-methylureido, 3,3-dimethylureido, and 3-phenylureido.
- alkoxy groups for use herein include, by way of example, an alkyl group as defined above attached via oxygen linkage to the rest of the molecule, i.e., of the general formula -OR 2 9, wherein R 2 9 is an alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, aryl or an arylalkyl as defined above, e.g., -OCH 3 , -OC 2 H 5 , or -OC 6 H 5 , and the like.
- cycloalkyl groups for use herein include, by way of example, a substituted or unsubstituted non-aromatic mono or multicyclic ring system of about 3 to about 18 carbon atoms such as, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, perhydronapththyl, adamantyl and norbornyl groups bridged cyclic group or spirobicyclic groups, e.g., sprio-(4,4)-non-2-yl and the like, optionally containing one or more heteroatoms, e.g., O and N, and the like.
- cycloalkylalkyl groups for use herein include, by way of example, a substituted or unsubstituted cyclic ring-containing radical containing from about 3 to about 18 carbon atoms directly attached to the alkyl group which are then attached to the main structure of the monomer at any carbon from the alkyl group that results in the creation of a stable structure such as, for example, cyclopropylmethyl, cyclobutylethyl, cyclopentylethyl and the like, wherein the cyclic ring can optionally contain one or more heteroatoms, e.g., O and N, and the like.
- a substituted or unsubstituted cyclic ring-containing radical containing from about 3 to about 18 carbon atoms directly attached to the alkyl group which are then attached to the main structure of the monomer at any carbon from the alkyl group that results in the creation of a stable structure such as, for example, cyclopropylmethyl, cyclobutyleth
- cycloalkenyl groups for use herein include, by way of example, a substituted or unsubstituted cyclic ring-containing radical containing from about 3 to about 18 carbon atoms with at least one carbon-carbon double bond such as, for example, cyclopropenyl, cyclobutenyl, cyclopentenyl and the like, wherein the cyclic ring can optionally contain one or more heteroatoms, e.g., O and N, and the like.
- aryl groups for use herein include, by way of example, a substituted or unsubstituted monoaromatic or polyaromatic radical containing from about 5 to about 25 carbon atoms such as, for example, phenyl, naphthyl, tetrahydronapthyl, indenyl, biphenyl and the like, optionally containing one or more heteroatoms, e.g., O and N, and the like.
- arylalkyl groups for use herein include, by way of example, a substituted or unsubstituted aryl group as defined above directly bonded to an alkyl group as defined above, e.g., -CHaCnH 5 , -C 2 H 5 C 6 H 5 and the like, wherein the aryl group can optionally contain one or more heteroatoms, e.g., O and N, and the like.
- fluoroaryl groups for use herein include, by way of example, an aryl group as defined above having one or more fluorine atoms attached to the aryl group.
- heterocyclic ring groups for use herein include, by way of example, a substituted or unsubstituted stable 3 to about 15 membered ring radical, containing carbon atoms and from one to five heteroatoms, e.g., nitrogen, phosphorus, oxygen, sulfur and mixtures thereof.
- Suitable heterocyclic ring radicals for use herein may be a monocyclic, bicyclic or tricyclic ring system, which may include fused, bridged or spiro ring systems, and the nitrogen, phosphorus, carbon, oxygen or sulfur atoms in the heterocyclic ring radical may be optionally oxidized to various oxidation states.
- the nitrogen atom may be optionally quaternized; and the ring radical may be partially or fully saturated (i.e., heteroaromatic or heteroaryl aromatic).
- heterocyclic ring radicals include, but are not limited to, azetidinyl, acridinyl, benzodioxolyl, benzodioxanyl, benzofurnyl, carbazolyl, cinnolinyl, dioxolanyl, indolizinyl, naphthyridinyl, perhydroazepinyl, phenazinyl, phenothiazinyl, phenoxazinyl, phthalazinyl, pyridyl, pteridinyl, purinyl, quinazolinyl, quinoxalinyl, quinolinyl, isoquinolinyl, tetrazoyl, imidazolyl, tetrahydroisouino
- heteroaryl groups for use herein include, by way of example, a substituted or unsubstituted heterocyclic ring radical as defined above.
- the heteroaryl ring radical may be attached to the main structure at any heteroatom or carbon atom that results in the creation of a stable structure.
- heteroarylalkyl groups for use herein include, by way of example, a substituted or unsubstituted heteroaryl ring radical as defined above directly bonded to an alkyl group as defined above.
- the heteroarylalkyl radical may be attached to the main structure at any carbon atom from the alkyl group that results in the creation of a stable structure.
- Representative examples of heterocyclo groups for use herein include, by way of example, a substituted or unsubstituted heterocylic ring radical as defined above.
- the heterocyclo ring radical may be attached to the main structure at any heteroatom or carbon atom that results in the creation of a stable structure.
- heterocycloalkyl groups for use herein include, by way of example, a substituted or unsubstituted heterocylic ring radical as defined above directly bonded to an alkyl group as defined above.
- the heterocycloalkyl radical may be attached to the main structure at carbon atom in the alkyl group that results in the creation of a stable structure.
- a polymerizable ethylenically unsaturated organic radicals include, by way of example, (meth)acrylate -containing radicals, (meth)acrylamide -containing radicals, vinylcarbonate-containing radicals, vinylcarbamate-containing radicals, styrene-containing radicals and the like.
- a polymerizable ethylenically unsaturated organic radical can be represented by the general formula:
- R 30 is independently hydrogen, fluorine, an alkyl radical having 1 to 6 carbon atoms, or a -CO-Y-R3 2 radical wherein Y is -O-, -S- or -NH- and R 32 is a divalent alkylene radical having 1 to about 10 carbon atoms; and R3 1 is hydrogen, fluorine or methyl.
- silicone materials are merely exemplary, and other materials for use as cationic substrates that can benefit by being stored in a solution containing an anionic polymer according to the present invention and have been disclosed in various publications and are being continuously developed for use in contact lenses and other medical devices can also be used.
- suitable cationic monomer materials have a molecular weight of about 600 grams per mole or less, and include a quaternary ammonium group or a tertiary amine group that can be protonated at a pH value of about 7.2 to about 7.4 (physiological pH values).
- Illustrative monomers include the tertiary C 1 -Ci O alkyl, C 2 -C 3 alkanol, and benzyl aminoethyl or N-morpholinoethyl esters of acrylates and methacrylates such as 2-dimethylaminoethyl methacrylate (DMEAM), 2-N-morpholinoethyl methacrylate (MEM), N,N-diethanolaminoethyl methacrylate, N,N-dimethoxyethylaminoethyl methacrylate, vinyl amine, aminostyrene, 2-vinyl pyridine, 4-vinyl pyridine, N-(2-vinyloxyethyl)piperidine and quaternary ammonium compounds such as 3-trimethylammonium-2-hydroxypropyl methacrylate chloride (TMAHPM), 2-trimethylammoniumethyl methacrylic hydroxide, 2- trimethylammoniumethyl acrylic hydroxide, 2-trimethyl
- the silicon-containing monomer will be added to the monomeric mixtures in a minor amount, e.g., an amount of no more than about 15 weight percent, based on the total weight of the monomeric mixture.
- the silicone -containing monomer is present in an amount ranging from about 0.1 to about 15 weight percent, based on the total weight of the monomeric mixture.
- Silicone hydrogels of this invention are typically formed by polymerizing a monomeric mixture containing at least a major amount of a non-silicone-containing monomer and a minor amount of a silicone -containing monomer employing conventional polymerization conditions well known by those of ordinary skill in the art, e.g., exposing the monomeric mixture to light radiation, such as visible light or UV radiation, to heat, or both, to induce polymerization Generally, polymerization can be carried out for about 15 minutes to about 72 hours under an inert atmosphere of, for example, nitrogen or argon. If desired, the resulting polymerization product can be dried under vacuum, e.g., for about 5 to about 72 hours or left in an aqueous solution prior to use.
- a polymerization initiator may be included in the monomeric mixture to facilitate the polymerization step.
- Representative free radical thermal polymerization initiators are organic peroxides such as, for example, acetal peroxide, lauroyl peroxide, decanoyl peroxide, stearoyl peroxide, benzoyl peroxide, tertiarylbutyl peroxypivalate, peroxydicarbonate, and the like and mixtures thereof.
- UV initiators are those known in the field such as, for example, benzoin methyl ether, benzoin ethyl ether, Darocure 1 173, 1 164, 2273, 1 1 16, 2959, 3331 (EM Industries) and Igracure 651 and 184 (Ciba-Geigy), and the like and mixtures thereof.
- the initiator will be employed in the monomeric mixture at a concentration at about 0.1 to about 5 percent by weight of the total mixture.
- Polymerization of the monomeric mixture is generally performed in the presence of a diluent.
- the diluent is generally removed after polymerization and replaced with water in extraction and hydration protocols well known to those skilled in the art.
- Representative diluents are diols, alcohols, alcohol/water mixtures, ethyleneglycol, glycerine, liquid polyethylene glycol, low molecular weight linear polyhydroxyethylmethacrylates, glycol esters of lactic acid, formamides, ketones, dialkylsulfoxides, butyl carbitol, and the like and mixtures thereof.
- the monomeric mixtures can further contain a hydrophobic monomer.
- Suitable hydrophobic monomers include ethylenically unsaturated hydrophobic monomers such as, for example, (meth)acrylate-containing hydrophobic monomers, N-alkyl (meth)acrylamide -containing hydrophobic monomers, vinylcarbonate-containing hydrophobic monomers, vinylcarbamate-containing hydrophobic monomers, fluoroalkyl (meth)acrylate -containing hydrophobic monomers, N-fluoroalkyl (meth)acrylamide- containing hydrophobic monomers, N-fluoroalkyl vinylcarbonate-containing hydrophobic monomers, N-fluoroalkyl vinylcarbamate-containing hydrophobic monomers, styrenic -containing hydrophobic monomers, polyoxypropylene (meth)acrylate-containing hydrophobic monomers and the like and mixtures thereof.
- a hydrophobic monomer is represented by Formula XXV:
- R 3 o is methyl or hydrogen;
- R 31 is -O- or -NH-;
- R 32 and R 34 are independently a divalent radical selected from the group consisting of -CH 2 -, -CHOH- and -CHR35-;
- R 34 and R 35 are independently a branched C 3 -C 8 alkyl group; and
- n is an integer of at least 1
- m and p are independently 0 or an integer of at least 1 , provided that the sum of m, p and n is 2, 3, 4 or 5.
- hydrophobic monomers include, but are not limited to, 4-t-butyl-2-hydroxycyclohexyl methacrylate (TBE); 4-t-butyl-2- hydroxycyclopentyl methacrylate; 4-t-butyl-2-hydroxycyclohexyl methacrylamide (TBA); ⁇ -isopentyl-S-hydroxycyclohexyl methacrylate; and 2-isohexyl-5- hydroxycyclopentyl methacrylamide.
- TBE 4-t-butyl-2-hydroxycyclohexyl methacrylate
- TBA 4-t-butyl-2- hydroxycyclopentyl methacrylamide
- TBA 2-isopentyl-S-hydroxycyclohexyl methacrylamide
- 2-isohexyl-5- hydroxycyclopentyl methacrylamide 2-isohexyl-5- hydroxycyclopentyl methacrylamide.
- Preferred hydrophobic monomers include TBE and TBA.
- the hydrophobic monomer will ordinarily be present in the monomeric mixtures in an amount ranging from 0 to about 15 weight percent, based on the total weight of the monomeric mixtures.
- the monomeric mixture may also include a crosslinking agent.
- a crosslinking agent typically, either the non-silicone-containing hydrophilic monomer or silicone -containing monomer functions as a crosslinking agent (a crosslinker being defined as a monomer having multiple polymerizable functionalities) or a separate crosslinker may be employed.
- Crosslinking agents are known in the art, and representative crosslinking agents include allyl methacrylate and ethylene glycol dimethacrylate (EGDMA).
- EGDMA ethylene glycol dimethacrylate
- crosslinkers such as methacryloxyethyl vinyl carbonate (HEMAVC), 4- vinylphenyl vinyl carbonate, and 4-vinylphenyl carbamate are used.
- the monomeric mixture may also include a strengthening monomer.
- strengthening monomer as used here relates to a monomer which can be polymerized with hydrophilic monomers in order to provide polymeric materials with improved physical properties, particularly tear and tensile strength. It is understood that the additional hydrophilic monomer is defined as different from, or exclusive of, the strengthening monomer.
- the strengthening monomer will ordinarily be present in the monomeric mixture in an amount ranging from about 0.01 to about 20 weight percent and preferably from about 5 to about 10 weight percent, based on the total weight of the monomeric mixture.
- the monomeric mixture may include a tinting agent, defined as an agent that, when incorporated in the final lens, imparts some degree of color to the lens.
- tinting agents are known in the art, including non-polymerizable agents, or polymerizable agents that include an activated unsaturated group that is reactive with the lens-forming monomers.
- This latter class is the compound 1,4- bis(4-(2-methacryloxyethyl)phenylamino)anthraquinone, a blue visibility-tinting agent disclosed in U.S. Patent No. 4,997,897.
- the hydrogel materials of the present invention have a water content of greater than 50% water.
- the high water content hydrogel materials of the present invention will have a water content of at least about 70% water.
- the high water content hydrogel materials of the present invention will have a water content of at least about 80% water.
- the high water content silicone hydrogels of the present invention can have an oxygen permeability of about 30 Barrers to about 70 Barrers and preferably from about 40 Barrers to about 60 Barrers. It is also preferred that the hydrogel materials have a water contact angle of less than about 90 degrees.
- the hydrogel materials are suitable for biomedical applications.
- shaped articles for use in biomedical applications or “biomedical devices or materials” mean the hydrogel materials disclosed herein have physicochemical properties rendering them suitable for prolonged contact with living tissue, blood and the mucous membranes.
- contact lenses can be obtained by charging the monomer mixtures to a mold, and then subjecting it to the light radiation or heat to effect curing of the monomer mixture in the mold.
- Various processes are known for curing a monomeric mixture in the production of contact lenses, including spincasting and static casting.
- Spincasting methods involve charging the monomer mixture to a mold, and spinning the mold in a controlled manner while exposing the monomer mixture to light.
- Static casting methods involve charging the monomer mixture between two mold sections, one mold section shaped to form the anterior lens surface and the other mold section shaped to form the posterior lens surface, and curing the monomer mixture by exposure to light.
- Such methods are described in U.S. Pat. Nos. 3,408,429, 3,660,545, 4, 113,224, 4,197,266, and 5,271,875.
- the monomer mixtures may be cast in the shape of rods or buttons, which are then lathe cut into a desired lens shape.
- Modulus may be measured with an Instron (Model 4502) instrument according to ASTM D- 1708a, where the hydrogel copolymer film sample is immersed in borate buffered saline.
- An appropriate size of the film sample is gauge length 22 mm and width 4.75 mm, where the sample further has ends forming a dogbone shape to accommodate gripping of the sample with clamps of the Instron instrument, and a thickness of 100+50 microns.
- the water content of the hydrated films was measured per a gravimetric method.
- Two sets of fully hydrated lenses containing 5 lenses per set are removed from their storage device. The lenses are blotted with filter paper to remove residual surface water. Each set is then individually weighed to determine the "wet weight”.
- the two sets of lenses are then placed in a 500 to 650 watt microwave oven on a high setting for a period of 10 minutes. The two sets of lenses are then removed from the microwave and each set is weighed individually to determine a "dry weight”.
- the % water content for each set is determined using the equation below. The reported water content represents the average of the two sets.
- Oxygen permeability (also referred to as Dk) was determined by the following procedure. Other methods and/or instruments may be used as long as the oxygen permeability values obtained therefrom are equivalent to the described method.
- the oxygen permeability of silicone hydrogels is measured by the polarographic method (ANSI Z80.20-1998) using an O2 Permeometer Model 20 IT instrument (Createch, Albany, California USA) having a probe containing a central, circular gold cathode at its end and a silver anode insulated from the cathode. Measurements are taken only on pre- inspected pinhole-free, flat silicone hydrogel film samples of three different center thicknesses ranging from 150 to 600 microns. Center thickness measurements of the film samples may be measured using a Rehder ET-I electronic thickness gauge.
- the film samples have the shape of a circular disk. Measurements are taken with the film sample and probe immersed in a bath containing circulating phosphate buffered saline (PBS) equilibrated at 35 0 C+/- 0.2°. Prior to immersing the probe and film sample in the PBS bath, the film sample is placed and centered on the cathode premoistened with the equilibrated PBS, ensuring no air bubbles or excess PBS exists between the cathode and the film sample, and the film sample is then secured to the probe with a mounting cap, with the cathode portion of the probe contacting only the film sample.
- PBS circulating phosphate buffered saline
- Teflon polymer membrane e.g., having a circular disk shape
- the Teflon membrane is first placed on the pre-moistened cathode, and then the film sample is placed on the Teflon membrane, ensuring no air bubbles or excess PBS exists beneath the Teflon membrane or film sample.
- oxygen permeability is calculated from the film samples having at least three different thicknesses. Any film samples hydrated with solutions other than PBS are first soaked in purified water and allowed to equilibrate for at least 24 hours, and then soaked in PHB and allowed to equilibrate for at least 12 hours. The instruments are regularly cleaned and regularly calibrated using RGP standards. Upper and lower limits are established by calculating a +/- 8.8% of the Repository values established by William J. Benjamin, et al., The Oxygen Permeability of Reference Materials, Optom Vis Sci 7 (12s): 95 ( 1997), the disclosure of which is incorporated herein in its entirety:
- EXAMPLE 1 A base formulation was prepared containing N-vinyl-2-pyrrolidone (NVP) (90 weight percent) and 4-t-butyl-2-hydroxycyclohexyl methacrylate (TBE) (10 weight percent). To this formulation was added ethylene glycol dimethacrylate (EGDMA) (0.15 weight percent), 2-hydroxyethyl methacrylate (HEMA) vinyl carbonate (0.15 weight percent) and a cationic silicone based tris-methacrylate of the general structure as defined in Formula VII (5 weight percent) and VazoTM 64 (azo bis-isobutylnitrile (AIBN)) (0.5 weight percent). The resultant mixture was thermally cured for about 3 hours. The resulting film had a modulus of 40 g/mm 2 , a water content of 83% and a Dk of 51 barrers.
- NDP N-vinyl-2-pyrrolidone
- TBE 4-t-butyl-2-hydroxycyclohexyl methacrylate
- a base formulation was prepared containing NVP (90 weight percent) and TBE (10 weight percent). To this formulation was added HEMA vinyl carbonate (0.30 weight percent), a silicone based methacrylate (15 weight percent) and AIBN (0.5 weight percent). The resultant monomeric mixture was thermally cured for about 3 hours. The resulting film had a modulus of 52 g/mm 2 , a water content of 79% and a Dk of 42 barrers.
- the silicone based methacrylate used in this example is of the formula:
- a base formulation was prepared containing NVP (90 weight percent) and TBE (5 weight percent). To this formulation was added allyl methacrylate (0.38 weight percent), ethyleneglycol dimethacrylate (EGDMA) (0.38 weight percent), tris(trimethoxysilylpropyl methacrylate (TRIS-MA)(5 weight percent) and AIBN (0.5 weight percent). The resultant monomeric mixture was thermally cured for about 3 hours. The resulting lens had a modulus of -50 g/mm , a water content of -78% and a Dk of -42 barrers.
- a base formulation was prepared containing NVP (90 weight percent) and TBE
- the resultant monomeric mixture was thermally cured for about 3 hours.
- the resulting lens had a modulus of -80 g/mm 2 , a water content of -79% and a Dk of -45 barrers.
- a base formulation was prepared containing NVP (90 weight percent) and TBE ( 10 weight percent). To this formulation was added allyl methacrylate (0.38 weight percent), ethyleneglycol dimethacrylate (EGDMA) (0.38 weight percent), a monomethacryloxypropyl terminated polydimethylsiloxane(5 weight percent) and AIBN (0.5 weight percent). The resultant monomeric mixture was thermally cured for about 3 hours.
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Eyeglasses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
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Abstract
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Claims
Priority Applications (1)
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EP20110181088 EP2397505A1 (en) | 2007-12-03 | 2008-11-12 | High water content silicone hydrogels |
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US99178307P | 2007-12-03 | 2007-12-03 | |
US12/267,660 US7934830B2 (en) | 2007-12-03 | 2008-11-10 | High water content silicone hydrogels |
PCT/US2008/083160 WO2009073321A1 (en) | 2007-12-03 | 2008-11-12 | High water content silicone hydrogels |
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EP2222736A1 true EP2222736A1 (en) | 2010-09-01 |
EP2222736B1 EP2222736B1 (en) | 2011-09-21 |
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EP20080858010 Active EP2222736B1 (en) | 2007-12-03 | 2008-11-12 | High water content silicone hydrogels |
EP20110181088 Withdrawn EP2397505A1 (en) | 2007-12-03 | 2008-11-12 | High water content silicone hydrogels |
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EP20110181088 Withdrawn EP2397505A1 (en) | 2007-12-03 | 2008-11-12 | High water content silicone hydrogels |
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US (1) | US7934830B2 (en) |
EP (2) | EP2222736B1 (en) |
JP (1) | JP2011505486A (en) |
CN (1) | CN101883799B (en) |
AT (1) | ATE525407T1 (en) |
ES (1) | ES2370460T3 (en) |
WO (1) | WO2009073321A1 (en) |
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- 2008-11-10 US US12/267,660 patent/US7934830B2/en active Active
- 2008-11-12 JP JP2010536961A patent/JP2011505486A/en active Pending
- 2008-11-12 ES ES08858010T patent/ES2370460T3/en active Active
- 2008-11-12 EP EP20080858010 patent/EP2222736B1/en active Active
- 2008-11-12 AT AT08858010T patent/ATE525407T1/en not_active IP Right Cessation
- 2008-11-12 EP EP20110181088 patent/EP2397505A1/en not_active Withdrawn
- 2008-11-12 WO PCT/US2008/083160 patent/WO2009073321A1/en active Application Filing
- 2008-11-12 CN CN2008801189920A patent/CN101883799B/en active Active
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CN101883799B (en) | 2013-03-27 |
US20090141234A1 (en) | 2009-06-04 |
EP2222736B1 (en) | 2011-09-21 |
ES2370460T3 (en) | 2011-12-16 |
US7934830B2 (en) | 2011-05-03 |
EP2397505A1 (en) | 2011-12-21 |
CN101883799A (en) | 2010-11-10 |
ATE525407T1 (en) | 2011-10-15 |
WO2009073321A1 (en) | 2009-06-11 |
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